JP2009209326A - Fragrance composition - Google Patents
Fragrance composition Download PDFInfo
- Publication number
- JP2009209326A JP2009209326A JP2008056542A JP2008056542A JP2009209326A JP 2009209326 A JP2009209326 A JP 2009209326A JP 2008056542 A JP2008056542 A JP 2008056542A JP 2008056542 A JP2008056542 A JP 2008056542A JP 2009209326 A JP2009209326 A JP 2009209326A
- Authority
- JP
- Japan
- Prior art keywords
- group
- fragrance
- ethyl
- isopropyl
- cis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003205 fragrance Substances 0.000 title claims abstract description 49
- 239000000203 mixture Substances 0.000 title claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 4
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000796 flavoring agent Substances 0.000 claims description 3
- 235000019634 flavors Nutrition 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 4
- -1 ester compound Chemical class 0.000 description 48
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 150000002430 hydrocarbons Chemical group 0.000 description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000002304 perfume Substances 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 5
- KXMPKKAYNBSWSH-UHFFFAOYSA-N ethyl 1-methyl-4-propan-2-ylcyclohexane-1-carboxylate Chemical compound CCOC(=O)C1(C)CCC(C(C)C)CC1 KXMPKKAYNBSWSH-UHFFFAOYSA-N 0.000 description 5
- AZFUREKVEIYHGX-UHFFFAOYSA-N methyl 1-methyl-4-propan-2-ylcyclohexane-1-carboxylate Chemical compound COC(=O)C1(C)CCC(C(C)C)CC1 AZFUREKVEIYHGX-UHFFFAOYSA-N 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 3
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 3
- VOVPSLMZFGVAIS-UHFFFAOYSA-N 1-methyl-4-propan-2-ylcyclohexane-1-carboxylic acid Chemical compound CC(C)C1CCC(C)(C(O)=O)CC1 VOVPSLMZFGVAIS-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- 241000207199 Citrus Species 0.000 description 3
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 235000020971 citrus fruits Nutrition 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- ZNJFBWYDHIGLCU-HWKXXFMVSA-N (-)-Jasmonic acid Natural products CC\C=C/C[C@@H]1[C@@H](CC(O)=O)CCC1=O ZNJFBWYDHIGLCU-HWKXXFMVSA-N 0.000 description 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- LOKPJYNMYCVCRM-UHFFFAOYSA-N 16-Hexadecanolide Chemical compound O=C1CCCCCCCCCCCCCCCO1 LOKPJYNMYCVCRM-UHFFFAOYSA-N 0.000 description 2
- UIERETOOQGIECD-ARJAWSKDSA-M 2-Methyl-2-butenoic acid Natural products C\C=C(\C)C([O-])=O UIERETOOQGIECD-ARJAWSKDSA-M 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- INAXVXBDKKUCGI-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylfuran-3-one Chemical compound CC1OC(C)=C(O)C1=O INAXVXBDKKUCGI-UHFFFAOYSA-N 0.000 description 2
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 2
- GHBSPIPJMLAMEP-UHFFFAOYSA-N 6-pentyloxan-2-one Chemical compound CCCCCC1CCCC(=O)O1 GHBSPIPJMLAMEP-UHFFFAOYSA-N 0.000 description 2
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
- DZNVIZQPWLDQHI-UHFFFAOYSA-N Citronellyl formate Chemical compound O=COCCC(C)CCC=C(C)C DZNVIZQPWLDQHI-UHFFFAOYSA-N 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- KGEKLUUHTZCSIP-HOSYDEDBSA-N [(1s,4s,6r)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-HOSYDEDBSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- IGODOXYLBBXFDW-UHFFFAOYSA-N alpha-Terpinyl acetate Chemical compound CC(=O)OC(C)(C)C1CCC(C)=CC1 IGODOXYLBBXFDW-UHFFFAOYSA-N 0.000 description 2
- 238000003287 bathing Methods 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229930016911 cinnamic acid Natural products 0.000 description 2
- 235000013985 cinnamic acid Nutrition 0.000 description 2
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- HCRBXQFHJMCTLF-ZCFIWIBFSA-N ethyl (2r)-2-methylbutanoate Chemical compound CCOC(=O)[C@H](C)CC HCRBXQFHJMCTLF-ZCFIWIBFSA-N 0.000 description 2
- PZUDDXJZNSJESK-UHFFFAOYSA-N ethyl 2-cyclohexylpropanoate Chemical compound CCOC(=O)C(C)C1CCCCC1 PZUDDXJZNSJESK-UHFFFAOYSA-N 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 2
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- ZNJFBWYDHIGLCU-UHFFFAOYSA-N jasmonic acid Natural products CCC=CCC1C(CC(O)=O)CCC1=O ZNJFBWYDHIGLCU-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- FRISMOQHTLZZRP-UHFFFAOYSA-N nerol oxide Chemical compound CC(C)=CC1CC(C)=CCO1 FRISMOQHTLZZRP-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
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- 150000003902 salicylic acid esters Chemical class 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
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- 239000000341 volatile oil Substances 0.000 description 2
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 2
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 2
- FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 description 1
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 1
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- WTOYNNBCKUYIKC-JMSVASOKSA-N (+)-nootkatone Chemical compound C1C[C@@H](C(C)=C)C[C@@]2(C)[C@H](C)CC(=O)C=C21 WTOYNNBCKUYIKC-JMSVASOKSA-N 0.000 description 1
- QEBNYNLSCGVZOH-NFAWXSAZSA-N (+)-valencene Chemical compound C1C[C@@H](C(C)=C)C[C@@]2(C)[C@H](C)CCC=C21 QEBNYNLSCGVZOH-NFAWXSAZSA-N 0.000 description 1
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- GEWDNTWNSAZUDX-WQMVXFAESA-N (-)-methyl jasmonate Chemical compound CC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-WQMVXFAESA-N 0.000 description 1
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
Abstract
Description
本発明は、調合香料原料として有用なエステル化合物を含有する香料組成物に関する。 The present invention relates to a fragrance composition containing an ester compound useful as a blended fragrance material.
特許文献１には４−イソプロピルシクロヘキサンカルボン酸エステルが従来から香料分野で利用されていることが記載されているが、その匂いについては記載されていない。また、特許文献２によれば、シクロヘキサンカルボン酸エステルの４位に加え１位もアルキル置換されたカルボン酸エステルとして、１，４−ジメチルシクロヘキサンカルボン酸エステルが有用な香料素材であることが知られており、その香気はフレッシュなハーバル香をグリーン及びフローラルな香調と共にもつと記載されている。
また、非特許文献１には、４−アルキル−１−メチルシクロヘキサンカルボン酸エチル類が、非特許文献２には４−イソプロピル−１−メチルシクロヘキサンカルボン酸エチルが記載されているが、いずれもその匂いについては記載されていない。
Patent Document 1 describes that 4-isopropylcyclohexanecarboxylic acid ester is conventionally used in the perfume field, but does not describe the odor. Further, according to Patent Document 2, it is known that 1,4-dimethylcyclohexanecarboxylic acid ester is a useful perfume material as a carboxylic acid ester in which the 1-position is substituted with alkyl in addition to the 4-position of cyclohexanecarboxylic acid ester. The fragrance is described as having a fresh herbal scent with green and floral scents.
Non-patent document 1 describes ethyl 4-alkyl-1-methylcyclohexanecarboxylates, and Non-patent document 2 describes ethyl 4-isopropyl-1-methylcyclohexanecarboxylate. The smell is not described.
本発明の課題は、従来知られていない特徴的で新鮮な木や花や草葉のニュアンスを持ち、さまざまな香料と調和して調合香料をより洗練された香りに変えることができるフルーティー香料素材としての香料組成物を提供することにある。 The subject of the present invention is a fruity fragrance material that has a characteristic and fresh nuance of trees, flowers, and leaves that can not be known in the past, and that can change the blended fragrance into a more sophisticated fragrance in harmony with various fragrances. It is in providing the fragrance | flavor composition of.
本発明者らは、上記課題を解決すべく１位と４位に炭化水素基を有する種々のシクロヘキサンカルボン酸エステルの香気について検討した結果、シクロヘキサン環の４位に炭素数２〜４の炭化水素基を有し、１位に炭素数１〜４の炭化水素基を有するシクロヘキサンカルボン酸エステル類が、特徴的な木や花や草葉のニュアンスを持つフルーティー香気を有し、上記課題を解決できることを見出した。
すなわち、本発明は、下記一般式（Ｉ）で表される化合物を含有する香料組成物に関する。
In order to solve the above problems, the present inventors have studied the fragrances of various cyclohexanecarboxylic acid esters having a hydrocarbon group at the 1-position and the 4-position, and as a result, the hydrocarbon having 2 to 4 carbon atoms at the 4-position of the cyclohexane ring. A cyclohexanecarboxylic acid ester having a group and a C1-C4 hydrocarbon group at the 1-position has a fruity aroma with a characteristic nuance of trees, flowers and leaves, and can solve the above problems I found it.
That is, this invention relates to the fragrance | flavor composition containing the compound represented by the following general formula (I).
本発明によれば、トイレタリー用品等への賦香成分として有用な、上記一般式（１）であらわされる脂環式エステルを含有することで、洗練された香調が賦与された香料組成物を提供することができる。 According to the present invention, there is provided a fragrance composition having a refined fragrance tone by containing an alicyclic ester represented by the above general formula (1), which is useful as a fragrance component for toiletries and the like. Can be provided.
［本発明の脂環式エステル］
本発明の香料組成物は、下記一般式（Ｉ）で表される脂環式エステル（本明細書において、「本発明の脂環式エステル」ということがある）を含有する。
The perfume composition of the present invention contains an alicyclic ester represented by the following general formula (I) (in the present specification, sometimes referred to as “the alicyclic ester of the present invention”).
一般式（Ｉ）において、Ｒ1は炭素数１〜４の炭化水素基を表す。Ｒ1で表わされる炭化水素基としては、具体的には、それぞれ炭素数１〜４の、アルキル基、アルケニル基、及びアルキニル基が好ましく挙げられ、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基などののアルキル基、ビニル基、アリル基、１−ブテニル基、１−メチルビニル基等のアルケニル基、エチニル基、２−プロピニル基等のアルキニル基が挙げられる。
Ｒ1としては香調の観点から、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ−ブチル基がより好ましく、メチル基、エチル基、プロピル基、イソプロピル基がさらに好ましく、メチル基、エチル基が特に好ましい。
In formula (I), R 1 represents a hydrocarbon group having 1 to 4 carbon atoms. Specific examples of the hydrocarbon group represented by R 1 include preferably an alkyl group, an alkenyl group, and an alkynyl group each having 1 to 4 carbon atoms, such as a methyl group, an ethyl group, a propyl group, and an isopropyl group. Group, alkyl group such as butyl group, isobutyl group, sec-butyl group and tert-butyl group, alkenyl group such as vinyl group, allyl group, 1-butenyl group and 1-methylvinyl group, ethynyl group and 2-propynyl And alkynyl groups such as groups.
R 1 is more preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, or a sec-butyl group, and more preferably a methyl group, an ethyl group, a propyl group, or an isopropyl group from the viewpoint of fragrance. A methyl group and an ethyl group are particularly preferable.
一般式（Ｉ）において、Ｒ2は炭素数１〜４の炭化水素基を表す。Ｒ2で表わされる炭化水素基としては、具体的には、それぞれ炭素数１〜４の、アルキル基、アルケニル基、及びアルキニル基が好ましく挙げられ、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基などのアルキル基、ビニル基、アリル基、１−ブテニル基、１−メチルビニル基等のアルケニル基、エチニル基、２−プロピニル基等のアルキニル基が挙げられる。
Ｒ2としては香調の観点から、メチル基、エチル基、プロピル基、イソプロピル基、ビニル基、アリル基がより好ましく、メチル基、エチル基、プロピル基、ビニル基、アリル基がさらに好ましく、メチル基、エチル基が特に好ましい。
In the general formula (I), R 2 represents a hydrocarbon group having 1 to 4 carbon atoms. Specific examples of the hydrocarbon group represented by R 2 include preferably an alkyl group, an alkenyl group, and an alkynyl group each having 1 to 4 carbon atoms, such as a methyl group, an ethyl group, a propyl group, and an isopropyl group. Group, butyl group, isobutyl group, sec-butyl group, tert-butyl group and other alkyl groups, vinyl group, allyl group, 1-butenyl group, 1-methylvinyl group and other alkenyl groups, ethynyl group, 2-propynyl group And alkynyl groups such as
R 2 is more preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a vinyl group or an allyl group, more preferably a methyl group, an ethyl group, a propyl group, a vinyl group or an allyl group from the viewpoint of fragrance. A group and an ethyl group are particularly preferred.
一般式（Ｉ）において、Ｒ3は炭素数２〜４の炭化水素基を表す。Ｒ3で表わされる炭化水素基としては、具体的には、それぞれ炭素数２〜４の、アルキル基、アルケニル基、及びアルキニル基が好ましく挙げられ、例えば、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基などのアルキル基、ビニル基、アリル基、１−ブテニル基、１−メチルビニル基等のアルケニル基、エチニル基、２−プロピニル基等のアルキニル基が挙げられる。
Ｒ3としては香調の観点から、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、アリル基、１−メチルビニル基が好ましく、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ−ブチル基、１−メチルビニル基がより好ましく、イソプロピル基が特に好ましい。
In the general formula (I), R 3 represents a hydrocarbon group having 2 to 4 carbon atoms. Specific examples of the hydrocarbon group represented by R 3 preferably include an alkyl group, an alkenyl group, and an alkynyl group each having 2 to 4 carbon atoms, such as an ethyl group, a propyl group, an isopropyl group, and butyl. Group, alkyl group such as isobutyl group, sec-butyl group and tert-butyl group, alkynyl group such as vinyl group, allyl group, 1-butenyl group and 1-methylvinyl group, ethynyl group and 2-propynyl group Groups.
R 3 is preferably an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an allyl group, or a 1-methylvinyl group from the viewpoint of fragrance. Group, butyl group, isobutyl group, sec-butyl group and 1-methylvinyl group are more preferable, and isopropyl group is particularly preferable.
本発明の香料組成物に含まれる一般式（Ｉ）で表される化合物は、１位のＣＯＯＲ1基と４位の炭化水素基がシクロヘキサン環に対して立体的に同じ側にあるシス形を有するシス体と、反対側にあるトランス形を有するトランス体の混合物である場合がある。本発明によれば、甘さを含むフルーティー感がより強いトランス体の含有率が高いほど調合香料中での効果が高いため、これらの含有割合は、質量比で、シス体：トランス体＝９９：１〜０：１００であることが好ましく、９８：２〜０：１００がより好ましい。更に、シス体とトランス体の含有率は、工業的に有利な収率を達成しやすいという観点からは９８：２〜６０：４０であることが好ましく、９８：２〜９０：１０であることがより好ましい。このようなシス体、トランス体の存在及びその含有量は、例えばＮＭＲ及び／あるいはガスクロマトグラフィーにより測定することができる。 The compound represented by the general formula (I) contained in the fragrance composition of the present invention has a cis form in which the COOR 1 group at the 1-position and the hydrocarbon group at the 4-position are sterically on the same side with respect to the cyclohexane ring. It may be a mixture of a cis body having a trans form having a trans form on the opposite side. According to the present invention, the higher the content of the trans isomer having a stronger fruity feeling including sweetness, the higher the effect in the blended fragrance. Therefore, the content ratio is cis isomer: trans isomer = 99 in mass ratio. : 1 to 0: 100 is preferable, and 98: 2 to 0: 100 is more preferable. Furthermore, the content of the cis isomer and the trans isomer is preferably 98: 2 to 60:40, and preferably 98: 2 to 90:10, from the viewpoint of easily achieving an industrially advantageous yield. Is more preferable. The presence and content of such cis- and trans-isomers can be measured, for example, by NMR and / or gas chromatography.
［脂環式エステルの製造方法］
本発明の脂環式エステルは、例えばカナディアン・ジャーナル・オブ・ケミストリー 第７４巻２４８７−２５０２頁（１９９６年）記載の方法を用いて、下記反応式（Ａ）によって製造することができる。
[Method for producing alicyclic ester]
The alicyclic ester of the present invention can be produced, for example, according to the following reaction formula (A) using the method described in Canadian Journal of Chemistry, Volume 74, pages 2487-2502 (1996).
本発明の脂環式エステルはまた、下記反応式（Ｂ）に従ってアルデヒドを酸化剤で酸化してカルボン酸とした後に、Ｒ1ＯＨでエステル化することによって製造することもできる。
さらに、本発明の脂環式エステルは、Ｒ2がメチル基でＲ3がイソプロピル基の場合にはIzvestiya Akademii Nauk SSSR, Seriya Khimicheskaya第４号８４１−８４７頁（１９７９年）記載の方法に従って製造することもできる。
なお、上記式（Ａ）及び（Ｂ）の各々において、Ｒ1、Ｒ2及びＲは3いずれも前記一般式（１）におけるものと同義である。
Furthermore, the alicyclic ester of the present invention is produced according to the method described in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya No. 4, pages 841-847 (1979) when R 2 is a methyl group and R 3 is an isopropyl group. You can also
Note that in each of the above formulas (A) and (B), R 1, R 2 and R have the same meanings as in any 3 Formula (1).
本発明の脂環式エステルは、特徴的で新鮮な木や花や草葉のニュアンスを持つフルーティー香気を有しかつ持続性にも優れることから、単独で又は他の成分と組み合わせて、石鹸、シャンプー、リンス、洗剤、化粧品、スプレー製品、芳香剤、香水、入浴剤等の賦香成分として使用できる。 The alicyclic ester of the present invention has a fruity fragrance with characteristic and fresh nuances of wood, flowers, and leaves, and also has excellent sustainability. Therefore, the alicyclic ester alone, or in combination with other ingredients, soap, shampoo , Rinse, detergent, cosmetics, spray products, fragrances, perfumes, bathing agents, etc.
［香料組成物］
本発明の香料組成物は、一般式（Ｉ）で表される脂環式エステルを含有するものであり、通常用いられる他の香料成分や、所望組成の調合香料に、一般式（Ｉ）で表される脂環式エステルを単独でまたは２種以上を組み合わせて配合して得られるものである。
その配合量は、調合香料の種類、目的とする香気の種類及び香気の強さ等により適宜選択することができるが、調合香料組成物中に０．０１〜１００質量％含有することが好ましく、０．１〜９０質量％含有することがより好ましく、０．１〜５０質量％含有することが更に好ましい。
[Perfume composition]
The fragrance composition of the present invention contains an alicyclic ester represented by the general formula (I), and other fragrance components that are usually used or a blended fragrance having a desired composition are represented by the general formula (I). The alicyclic ester represented can be obtained alone or in combination of two or more.
The blending amount can be appropriately selected depending on the type of the blended fragrance, the type of the target fragrance, the strength of the fragrance, etc., but is preferably contained in the blended fragrance composition in an amount of 0.01 to 100% by mass, It is more preferable to contain 0.1-90 mass%, and it is still more preferable to contain 0.1-50 mass%.
本発明の香料組成物において、脂環式エステルと組み合わせて用いることができる香料成分としては、炭化水素類、アルコール類、フェノール類、エステル類、カーボネート類、アルデヒド類、ケトン類、アセタール類、エーテル類、ニトリル類、カルボン酸類、ラクトン類、天然精油や天然抽出物等を挙げることができる。 In the fragrance composition of the present invention, the fragrance components that can be used in combination with the alicyclic ester include hydrocarbons, alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers. Nitriles, carboxylic acids, lactones, natural essential oils and natural extracts.
炭化水素類としては、リモネン、α−ピネン、β−ピネン、テルピネン、セドレン、ロンギフォレン、バレンセン等が挙げられる。
アルコール類としては、リナロール、シトロネロール、ゲラニオール、ネロール、テルピネオール、ジヒドロミルセノール、エチルリナロール、ファルネソール、ネロリドール、シス−３−ヘキセノール、セドロール、メントール、ボルネオール、フェニルエチルアルコール、ベンジルアルコール、ジメチルベンジルカルビノール、フェニルエチルジメチルカルビノール、フェニルヘキサノール、２，２，６−トリメチルシクロヘキシル−３−ヘキサノール、アンバーコア（花王株式会社商品名）等が挙げられる。
Examples of the hydrocarbons include limonene, α-pinene, β-pinene, terpinene, cedrene, longifolene, and valencene.
Alcohols include linalool, citronellol, geraniol, nerol, terpineol, dihydromyrcenol, ethyl linalool, farnesol, nerolidol, cis-3-hexenol, cedrol, menthol, borneol, phenylethyl alcohol, benzyl alcohol, dimethylbenzylcarbi Nol, phenylethyldimethylcarbinol, phenylhexanol, 2,2,6-trimethylcyclohexyl-3-hexanol, amber core (trade name of Kao Corporation) and the like.
フェノール類としては、グアヤコール、オイゲノール、イソオイゲノール、チモール、パラクレゾール、バニリン等が挙げられる。
エステル類としては、ギ酸エステル、酢酸エステル、プロピオン酸エステル、酪酸エステル、ノネン酸エステル、安息香酸エステル、桂皮酸エステル、サリチル酸エステル、ブラシル酸エステル、チグリン酸エステル、ジャスモン酸エステル、グリシド酸エステル、アントラニル酸エステル等が挙げられる。
Examples of phenols include guaiacol, eugenol, isoeugenol, thymol, paracresol, vanillin and the like.
Esters include formic acid ester, acetic acid ester, propionic acid ester, butyric acid ester, nonenic acid ester, benzoic acid ester, cinnamic acid ester, salicylic acid ester, brassylic acid ester, tiglic acid ester, jasmonic acid ester, glycidic acid ester, anthranil Acid ester etc. are mentioned.
ギ酸エステルとしては、リナリルホルメート、シトロネリルホルメート、ゲラニルホルメート等、酢酸エステルとしては、ヘキシルアセテート、シス−３−ヘキセニルアセテート、リナリルアセテート、シトロネリルアセテート、ゲラニルアセテート、ネリルアセテート、テルピニルアセテート、ノピルアセテート、ボルニルアセテート、イソボルニルアセテート、ｏ−ｔｅｒｔ−ブチルシクロヘキシルアセテート、ｐ−ｔｅｒｔ−ブチルシクロヘキシルアセテート、トリシクロデセニルアセテート、ベンジルアセテート、フェニルエチルアセテート、スチラリルアセテート、シンナミルアセテート、ジメチルベンジルカルビニルアセテート、フェニルエチルフェニルアセテート、３−ペンチルテトラヒドロピラン−４−イルアセテート等、パラクレジルフェニルアセテート、プロピオン酸エステルとしては、シトロネリルプロピオネート、トリシクロデセニルプロピオネート、アリルシクロヘキシルプロピオネート、エチル２−シクロヘキシルプロピオネート、ベンジルプロピオネート等、酪酸エステルとしては、シトロネリルブチレート、エチル２−メチルブチレート、ジメチルベンジルカルビニルブチレート、トリシクロデセニルイソブチレート等が挙げられる。 As formic acid ester, linalyl formate, citronellyl formate, geranyl formate, etc. As acetic acid ester, hexyl acetate, cis-3-hexenyl acetate, linalyl acetate, citronellyl acetate, geranyl acetate, neryl acetate, terpinyl Acetate, nopylacetate, bornyl acetate, isobornyl acetate, o-tert-butylcyclohexyl acetate, p-tert-butylcyclohexyl acetate, tricyclodecenyl acetate, benzyl acetate, phenylethyl acetate, styrylyl acetate, thinner Milacetate, dimethylbenzylcarbinyl acetate, phenylethylphenylacetate, 3-pentyltetrahydropyran-4-ylacetate, etc. Examples of lactic acid phenylacetate and propionate include citronellylpropionate, tricyclodecenylpropionate, allylcyclohexylpropionate, ethyl 2-cyclohexylpropionate, and benzylpropionate. , Citronellyl butyrate, ethyl 2-methylbutyrate, dimethylbenzylcarbyl butyrate, tricyclodecenyl isobutyrate and the like.
また、ノネン酸エステルとしては、メチル２−ノネノエート、エチル２−ノネノエート、エチル３−ノネノエート等、安息香酸エステルとしては、メチルベンゾエート、ベンジルベンゾエート、３，６−ジメチルベンゾエート等、メチルシンナメート、桂皮酸エステルとしては、ベンジルシンナメート等、サリチル酸エステルとしては、メチルサリシレート、ｎ−ヘキシルサリシレート、シス−３−ヘキセニルサリシレート、シクロヘキシルサリシレート、ベンジルサリシレート等が挙げられる。 Examples of the nonenoic acid ester include methyl 2-nonenoate, ethyl 2-nonenoate, and ethyl 3-nonenoate. Examples of the benzoic acid ester include methyl benzoate, benzyl benzoate, and 3,6-dimethyl benzoate. Examples of the ester include benzyl cinnamate, and examples of the salicylic acid ester include methyl salicylate, n-hexyl salicylate, cis-3-hexenyl salicylate, cyclohexyl salicylate, and benzyl salicylate.
さらに、ブラシル酸エステルとしては、エチレンブラシレート等、チグリン酸エステルとしては、ゲラニルチグレート、１−ヘキシルチグレート、シス−３−ヘキセニルチグレート等、ジャスモン酸エステルとしては、メチルジャスモネート、メチルジヒドロジャスモネート等、グリシド酸エステルとしては、メチル２，４−ジヒドロキシ−エチルメチルフェニルグリシデート、４−メチルフェニルエチルグリシデート等、アントラニル酸エステルとしては、メチルアントラニレート、エチルアントラニレート、ジメチルアントラニレート等が挙げられる。 Further, as the brassic acid ester, ethylene brushate, etc., as the tiglic acid ester, geranyl tiglate, 1-hexyl tiglate, cis-3-hexenyl tiglate, etc., as the jasmonic acid ester, methyl jasmonate, methyl Dihydrojasmonate, etc., as glycidic acid ester, methyl 2,4-dihydroxy-ethylmethylphenyl glycidate, 4-methylphenylethyl glycidate, etc., as anthranilic acid ester, methyl anthranilate, ethyl anthranilate, Examples include dimethyl anthranilate.
カーボネート類としては、ジャスマシクラット（花王株式会社商品名）、フロラマット（花王株式会社商品名）等が挙げられる。
その他のエステルとしては、ペラナット（花王株式会社商品名）、フルテート（花王株式会社商品名）、メルサット（花王株式会社商品名）、ポワレネート（花王株式会社商品名）等が挙げられる。
アルデヒド類としては、ｎ−オクタナール、n−ノナナール、ｎ−デカナ−ル、ｎ−ドデカナ−ル、２−メチルウンデカナール、１０−ウンデセナール、シトロネラール、シトラール、ヒドロキシシトロネラール、ベンズアルデヒド、フェニルアセトアルデヒド、フェニルプロピルアルデヒド、シンナミックアルデヒド、ジメチルテトラヒドロベンズアルデヒド、リラール（ＩＦＦ社、商品名）、２−シクロヘキシルプロパナール、ｐ−ｔｅｒｔ−ブチル−α−メチルヒドロシンナミックアルデヒド、ｐ−イソプロピル−α−メチルヒドロシンナミックアルデヒド、ｐ−エチル−α，α−ジメチルヒドロシンナミックアルデヒド、α−アミルシンナミックアルデヒド、α−ヘキシルシンナミックアルデヒド、ヘリオトロピン、α−メチル−３，４−メチレンジオキシヒドロシンナミックアルデヒド、ポレナールII（花王株式会社商品名）等が挙げられる。
Examples of carbonates include Jasma cyclat (trade name of Kao Corporation), Flora mat (trade name of Kao Corporation), and the like.
Other esters include Peranat (trade name of Kao Corporation), Full Tate (trade name of Kao Corporation), Mersat (trade name of Kao Corporation), Poirenate (trade name of Kao Corporation), and the like.
Examples of aldehydes include n-octanal, n-nonanal, n-decanal, n-dodecanal, 2-methylundecanal, 10-undecenal, citronellal, citral, hydroxycitronellal, benzaldehyde, phenylacetaldehyde, phenylpropional. Lualdehyde, cinnamic aldehyde, dimethyltetrahydrobenzaldehyde, Lilal (IFF, trade name), 2-cyclohexylpropanal, p-tert-butyl-α-methylhydrocinnamic aldehyde, p-isopropyl-α-methylhydrocinnamic Aldehyde, p-ethyl-α, α-dimethylhydrocinnamic aldehyde, α-amylcinnamic aldehyde, α-hexylcinnamic aldehyde, heliotropin, α-methyl-3,4- Chi dioxy hydro cinnamic aldehyde, Porenaru II (Kao Corporation trade name) and the like.
ケトン類としては、α−イオノン、β−イオノン、γ−イオノン、α−メチルイオノン、β−メチルイオノン、γ−メチルイオノン、ダマセノン、メチルヘプテノン、４−メチレン−３，５，６，６−テトラメチル−２−ヘプタノン、アミルシクロペンタノン、ジヒドロジャスモン、ローズケトン、カルボン、メントン、樟脳、アセチルセドレン、イソロンギフォラノン、ヌートカトン、ベンジルアセトン、アニシルアセトン、メチルβ−ナフチルケトン、２，５−ジメチル−４−ヒドロキシ−３（２Ｈ）−フラノン、マルトール、ムスコン、シベトン、シクロペンタデカノン等が挙げられる。 Examples of ketones include α-ionone, β-ionone, γ-ionone, α-methylionone, β-methylionone, γ-methylionone, damasenone, methylheptenone, 4-methylene-3,5,6,6-tetramethyl-2- Heptanone, amylcyclopentanone, dihydrojasmon, rose ketone, carvone, menthone, camphor, acetyl cedrene, isolongifolanone, nootkatone, benzylacetone, anisylacetone, methyl β-naphthylketone, 2,5-dimethyl-4 -Hydroxy-3 (2H) -furanone, maltol, muscone, sibeton, cyclopentadecanone and the like.
アセタール類としては、アセトアルデヒドエチルフェニルプロピルアセタール、シトラールジエチルアセタール、フェニルアセトアルデヒドグリセリンアセタール、エチルアセトアセテートエチレングリコールアセタール、ボアザンブレンフォルテ（花王株式会社商品名）等が挙げられる。
エーテル類としては、セドリルメチルエーテル、アネトール、β−ナフチルメチルエーテル、β−ナフチルエチルエーテル、リモネンオキサイド、ローズオキサイド、ネロールオキサイド、１，８−シネオール、ローズフラン、アンブロキサン（花王株式会社商品名）、ハーバベール（花王株式会社商品名）等が挙げられる。
ニトリル類としては、ゲラニルニトリル、シトロネリルニトリル、ドデカンニトリル等が挙げられる。
Examples of acetals include acetaldehyde ethylphenylpropyl acetal, citral diethyl acetal, phenylacetaldehyde glycerin acetal, ethyl acetoacetate ethylene glycol acetal, boazan brenforte (trade name of Kao Corporation), and the like.
Examples of ethers include cedol methyl ether, anethole, β-naphthyl methyl ether, β-naphthyl ethyl ether, limonene oxide, rose oxide, nerol oxide, 1,8-cineole, rose furan, ambroxan (product of Kao Corporation) Name) and Herbaval (trade name of Kao Corporation).
Examples of nitriles include geranyl nitrile, citronellyl nitrile, and dodecane nitrile.
カルボン酸類としては、安息香酸、フェニル酢酸、桂皮酸、ヒドロ桂皮酸、酪酸、２−ヘキセン酸等が挙げられる。
ラクトン類としては、γ−デカラクトン、δ−デカラクトン、γ−バレロラクトン、γ−ノナラクトン、γ−ウンデカラクトン、δ−ヘキサラクトン、γ−ジャスモラクトン、ウイスキーラクトン、クマリン、シクロペンタデカノリド、シクロヘキサデカノリド、アンブレットリド、１１−オキサヘキサデカノリド、ブチリデンフタリド等が挙げられる。
Examples of carboxylic acids include benzoic acid, phenylacetic acid, cinnamic acid, hydrocinnamic acid, butyric acid, and 2-hexenoic acid.
Examples of lactones include γ-decalactone, δ-decalactone, γ-valerolactone, γ-nonalactone, γ-undecalactone, δ-hexalactone, γ-jasmolactone, whiskey lactone, coumarin, cyclopentadecanolide, Examples include cyclohexadecanolide, ambretlide, 11-oxahexadecanolide, butylidenephthalide, and the like.
天然精油や天然抽出物としては、オレンジ、レモン、ライム、ベルガモット、バニラ、マンダリン、ペパーミント、スペアミント、ラベンダー、カモミル、ローズマリー、ユーカリ、セージ、バジル、ローズ、ロックローズ、ゼラニウム、ジャスミン、イランイラン、アニス、クローブ、ジンジャー、ナツメグ、カルダモン、セダー、ヒノキ、ベチバー、パチュリ、レモングラス、ラブダナム等が挙げられる。 Natural essential oils and natural extracts include orange, lemon, lime, bergamot, vanilla, mandarin, peppermint, spearmint, lavender, camomil, rosemary, eucalyptus, sage, basil, rose, rock rose, geranium, jasmine, ylang ylang, Anise, cloves, ginger, nutmeg, cardamom, cedar, cypress, vetiver, patchouli, lemongrass, lovedanum and the like.
実施例１
フラスコに４−イソプロピル−１−メチルシクロヘキサンカルバルデヒド１０ｇとｔｅｒｔ−ブタノール２００ｍＬと２−メチル−２−ブテン１００ｍＬを入れ、攪拌しながら０℃で亜塩素酸ナトリウム１３ｇとリン酸二水素ナトリウム１１ｇを８０ｍＬの水に溶解した溶液を加えた。室温で４０分攪拌後、ｔｅｒｔ−ブタノールを一部留去し、少量の硫酸を加えてからエーテルで抽出した溶液を濃縮、シリカゲルカラムで精製して４−イソプロピル−１−メチルシクロヘキサンカルボン酸１１ｇを得た。
Example 1
Place 10 g of 4-isopropyl-1-methylcyclohexanecarbaldehyde, 200 mL of tert-butanol, and 100 mL of 2-methyl-2-butene in a flask, and 80 mL of 13 g of sodium chlorite and 11 g of sodium dihydrogen phosphate at 0 ° C. with stirring. A solution dissolved in water was added. After stirring at room temperature for 40 minutes, part of tert-butanol was distilled off, a small amount of sulfuric acid was added, and the solution extracted with ether was concentrated and purified with a silica gel column to give 11 g of 4-isopropyl-1-methylcyclohexanecarboxylic acid. Obtained.
還流装置を付けたフラスコに、４−イソプロピル−１−メチルシクロヘキサンカルボン酸５ｇとエタノール６０ｍＬと硫酸１．５ｍＬを入れ、３４時間還流した。エタノールを留去してから水酸化ナトリウム水溶液を加えて酢酸エチルで抽出した溶液を濃縮、シリカゲルカラムで精製して４−イソプロピル−１−メチルシクロヘキサンカルボン酸エチル３ｇ［シス：トランス（質量比）＝９２：８］を得た。これを、さらにシリカゲルカラムあるいはガスクロマトグラフで分離して、シス−４−イソプロピル−１−メチルシクロヘキサンカルボン酸エチルとトランス−４−イソプロピルー１−メチルシクロヘキサンカルボン酸エチルを得た。
得られたシス−あるいはトランス−４−イソプロピル−１−メチルシクロヘキサンカルボン酸エチルの構造及び含有割合は、核磁気共鳴スペクトル（1Ｈ−ＮＭＲ）及びガスクロマトグラフィーにより同定及び測定した。核磁気共鳴スペクトルは、溶媒としてクロロホルム−ｄを用いて、Ｖａｒｉａｎ社製のＭｅｒｃｕｒｙ ４００により測定した。
A flask equipped with a reflux apparatus was charged with 5 g of 4-isopropyl-1-methylcyclohexanecarboxylic acid, 60 mL of ethanol, and 1.5 mL of sulfuric acid, and refluxed for 34 hours. Ethanol was distilled off, an aqueous sodium hydroxide solution was added, and the solution extracted with ethyl acetate was concentrated and purified with a silica gel column to obtain 3 g of ethyl 4-isopropyl-1-methylcyclohexanecarboxylate [cis: trans (mass ratio) = 92: 8]. This was further separated by a silica gel column or a gas chromatograph to obtain ethyl cis-4-isopropyl-1-methylcyclohexanecarboxylate and ethyl trans-4-isopropyl-1-methylcyclohexanecarboxylate.
The structure and content of the obtained ethyl cis- or trans-4-isopropyl-1-methylcyclohexanecarboxylate were identified and measured by nuclear magnetic resonance spectrum ( 1 H-NMR) and gas chromatography. The nuclear magnetic resonance spectrum was measured by Mercury 400 manufactured by Varian, using chloroform-d as a solvent.
シス−４−イソプロピル−１−メチルシクロヘキサンカルボン酸エチル
1H-NMR(CDCl3, 400MHz, δppm) : 0.83(d, J=6.4Hz, 6H), 0.96-1.11(m, 5H), 1.12 (s, 3H), 1.17(s, 3H), 1.25(t, J=6.8Hz, 3H), 1.35-1.39(m, 1H), 1.60(br d, J=8.0Hz, 2H), 2.21(br d, J=14.0Hz, 2H), 4.13(q, J=6.8Hz, 2H)
13C-NMR(CDCl3, 100MHz, δppm) : 14.7(CH3), 20.3(CH3), 27.6(CH2), 28.8(CH3), 33.1(CH), 36.5(CH2), 43.8(C), 43.8(CH), 60.4(CH2), 177.4(C)
匂い：軽いフルーティ、木様、緑の草葉様
Ethyl cis-4-isopropyl-1-methylcyclohexanecarboxylate
1 H-NMR (CDCl 3 , 400MHz, δppm): 0.83 (d, J = 6.4Hz, 6H), 0.96-1.11 (m, 5H), 1.12 (s, 3H), 1.17 (s, 3H), 1.25 ( t, J = 6.8Hz, 3H), 1.35-1.39 (m, 1H), 1.60 (br d, J = 8.0Hz, 2H), 2.21 (br d, J = 14.0Hz, 2H), 4.13 (q, J = 6.8Hz, 2H)
13 C-NMR (CDCl 3 , 100 MHz, δ ppm): 14.7 (CH 3 ), 20.3 (CH 3 ), 27.6 (CH 2 ), 28.8 (CH 3 ), 33.1 (CH), 36.5 (CH 2 ), 43.8 ( C), 43.8 (CH), 60.4 (CH 2 ), 177.4 (C)
Odor: light fruity, woody, green grassy
トランス−４−イソプロピル−１−メチルシクロヘキサンカルボン酸エチル
1H-NMR(CDCl3, 400MHz, δppm) : 0.87(d, J=6.8Hz, 6H), 0.97-1.06(m, 1H), 1.12-1.20(m, 2H), 1.17(s, 3H), 1.24(t, J=6.8Hz, 3H), 1.40-1.48(m, 1H), 1.54-1.60(m, 2H), 1.64-1.68(m, 4H), 4.11(q, J=6.8Hz, 2H)
13C-NMR(CDCl3, 100MHz, δppm) : 14.7(CH3), 20.3(CH3), 20.6(CH3), 25.1(CH2), 32.7(CH), 34.2(CH2), 42.1(C), 43.8(CH), 60.5(CH2), 179.1(C)
匂い：甘さを含む強いフルーティ、木様、緑の草葉様
Ethyl trans-4-isopropyl-1-methylcyclohexanecarboxylate
1 H-NMR (CDCl 3 , 400MHz, δppm): 0.87 (d, J = 6.8Hz, 6H), 0.97-1.06 (m, 1H), 1.12-1.20 (m, 2H), 1.17 (s, 3H), 1.24 (t, J = 6.8Hz, 3H), 1.40-1.48 (m, 1H), 1.54-1.60 (m, 2H), 1.64-1.68 (m, 4H), 4.11 (q, J = 6.8Hz, 2H)
13 C-NMR (CDCl 3 , 100 MHz, δ ppm): 14.7 (CH 3 ), 20.3 (CH 3 ), 20.6 (CH 3 ), 25.1 (CH 2 ), 32.7 (CH), 34.2 (CH 2 ), 42.1 ( C), 43.8 (CH), 60.5 (CH 2 ), 179.1 (C)
Smell: strong fruity, woody, green leaves like sweetness
実施例２
還流装置を付けたフラスコに、実施例１の前半部で得た４−イソプロピル−１−メチルシクロヘキサンカルボン酸４ｇとメタノール５０ｍＬと硫酸１ｍＬを入れ、２９時間還流した。メタノールを留去してから塩化メチレンと重曹を加えた後に、濾過、乾燥、濃縮を行い、シリカゲルカラムで精製して４−イソプロピル−１−メチルシクロヘキサンカルボン酸メチル３ｇ（シス：トランス＝９７：３）を得た。
Example 2
A flask equipped with a reflux apparatus was charged with 4 g of 4-isopropyl-1-methylcyclohexanecarboxylic acid obtained in the first half of Example 1, 50 mL of methanol and 1 mL of sulfuric acid, and refluxed for 29 hours. After distilling off the methanol, methylene chloride and sodium bicarbonate were added, followed by filtration, drying and concentration, purification on a silica gel column and 3 g of methyl 4-isopropyl-1-methylcyclohexanecarboxylate (cis: trans = 97: 3). )
４−イソプロピル−１−メチルシクロヘキサンカルボン酸メチル（シス：トランス＝９７：３の混合物）
1H-NMR(CDCl3, 400MHz, δppm, 混合物からの主な検出シグナル) : 0.83(d, J=6.8Hz), 0.87(d, J=6.8Hz), 0.96-1.11(m), 1.13 (s), 1.18(s), 1.21-1.48(m), 1.59-1.65(m), 2.20(br, d), 3.67(s)
13C-NMR(CDCl3, 100MHz, δppm, 混合物からの主な検出シグナル) : 20.0, 27.3, 28.4, 32.8, 36.2, 43.5, 43.7, 51.6, 117.6
匂い：新鮮で花様のフルーティ、緑の草葉様
Methyl 4-isopropyl-1-methylcyclohexanecarboxylate (mixture of cis: trans = 97: 3)
1 H-NMR (CDCl 3 , 400 MHz, δ ppm, main detection signal from the mixture): 0.83 (d, J = 6.8 Hz), 0.87 (d, J = 6.8 Hz), 0.96-1.11 (m), 1.13 ( s), 1.18 (s), 1.21-1.48 (m), 1.59-1.65 (m), 2.20 (br, d), 3.67 (s)
13 C-NMR (CDCl 3 , 100 MHz, δ ppm, main detection signal from the mixture): 20.0, 27.3, 28.4, 32.8, 36.2, 43.5, 43.7, 51.6, 117.6
Odor: fresh and flowery fruity, green grassy leaves
実施例３
実施例１で得られた４−イソプロピル−１−メチルシクロヘキサンカルボン酸エチル［シス：トランス（質量比）＝９２：８］を用いて、表１に示すように配合し香料組成物を調製した。なお、表１における各成分の配合量は質量部を表わす（以下同じ）。
Example 3
Using ethyl 4-isopropyl-1-methylcyclohexanecarboxylate [cis: trans (mass ratio) = 92: 8] obtained in Example 1, blended as shown in Table 1 to prepare a fragrance composition. In addition, the compounding quantity of each component in Table 1 represents a mass part (hereinafter the same).
比較例１
実施例３において、実施例１で得られた４−イソプロピル−１−メチルシクロヘキサンカルボン酸エチル［シス：トランス（質量比）＝９２：８］４０質量部に代えてジプロピレングリコール４０質量部を用いた以外は、実施例３と同様にして香料組成物を調製した。
Comparative Example 1
In Example 3, instead of 40 parts by mass of ethyl 4-isopropyl-1-methylcyclohexanecarboxylate [cis: trans (mass ratio) = 92: 8] obtained in Example 1, 40 parts by mass of dipropylene glycol was used. A fragrance composition was prepared in the same manner as in Example 3 except that.
比較例１に示したフルーティー調の香料組成物に対し、実施例１で得られた４−イソプロピル−１−メチルシクロヘキサンカルボン酸エチル［シス：トランス（質量比）＝９２：８］を配合した実施例３では、洋ナシ様のジューシーな甘さが強調され、果肉感をも想起させる優れた香気を有する調合香組成物が得られた。 Implementation of blending the fruity perfume composition shown in Comparative Example 1 with ethyl 4-isopropyl-1-methylcyclohexanecarboxylate [cis: trans (mass ratio) = 92: 8] obtained in Example 1 In Example 3, a pear-like juicy sweetness was emphasized, and a blended fragrance composition having an excellent fragrance reminiscent of fleshiness was obtained.
実施例４
実施例２で得られた４−イソプロピル−１−メチルシクロヘキサンカルボン酸メチル［シス：トランス（質量比）＝９7：３］を用いて、表２に示すように配合し香料組成物を調製した。
Example 4
Using the methyl 4-isopropyl-1-methylcyclohexanecarboxylate [cis: trans (mass ratio) = 97: 3] obtained in Example 2, blended as shown in Table 2 to prepare a fragrance composition.
比較例２
実施例４において、実施例２で得られた４−イソプロピル−１−メチルシクロヘキサンカルボン酸メチル［シス：トランス（質量比）＝９7：３］３０質量部に代えてジプロピレングリコール３０質量部を用いた以外は、実施例４と同様にして香料組成物を調製した。
Comparative Example 2
In Example 4, instead of 30 parts by mass of methyl 4-isopropyl-1-methylcyclohexanecarboxylate [cis: trans (mass ratio) = 97: 3] obtained in Example 2, 30 parts by mass of dipropylene glycol was used. A fragrance composition was prepared in the same manner as in Example 4 except that.
比較例２に示したシトラス・グリーン調の香料組成物に対し、実施例２で得られた４−イソプロピル−１−メチルシクロヘキサンカルボン酸メチル［シス：トランス（質量比）＝９７：３］を配合した実施例４では、フレッシュでみずみずしいシトラス香気が増強され、ユズ果実の香りを想起させる優れたシトラス・グリーン調の調合香料組成物が得られた。 To the citrus green tone fragrance composition shown in Comparative Example 2, methyl 4-isopropyl-1-methylcyclohexanecarboxylate [cis: trans (mass ratio) = 97: 3] obtained in Example 2 was blended. In Example 4, a fresh and fresh citrus fragrance was enhanced, and an excellent citrus green tone blended fragrance composition reminiscent of the scent of yuzu fruit was obtained.
本発明の香料組成物は、本発明の脂環式エステルを含有することで、洗練された香調が賦与され、石鹸、シャンプー、リンス、洗剤、化粧品、スプレー製品、芳香剤、香水、入浴剤等のトイレタリー用品等への賦香成分として好適に使用される。 The fragrance composition of the present invention contains the alicyclic ester of the present invention to give a refined fragrance, soap, shampoo, rinse, detergent, cosmetics, spray product, fragrance, perfume, bathing agent. It is suitably used as a perfuming ingredient for toiletries and the like.
Claims (2)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008056542A JP5270194B2 (en) | 2008-03-06 | 2008-03-06 | Fragrance composition |
| US12/921,287 US8383574B2 (en) | 2008-03-06 | 2009-03-02 | Perfume composition |
| ES09716480T ES2392318T3 (en) | 2008-03-06 | 2009-03-02 | Perfume composition |
| EP09716480A EP2253695B1 (en) | 2008-03-06 | 2009-03-02 | Perfume composition |
| PCT/JP2009/053887 WO2009110433A1 (en) | 2008-03-06 | 2009-03-02 | Perfume composition |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008056542A JP5270194B2 (en) | 2008-03-06 | 2008-03-06 | Fragrance composition |
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|---|---|
| JP2009209326A true JP2009209326A (en) | 2009-09-17 |
| JP5270194B2 JP5270194B2 (en) | 2013-08-21 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2008056542A Expired - Fee Related JP5270194B2 (en) | 2008-03-06 | 2008-03-06 | Fragrance composition |
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| Country | Link |
|---|---|
| US (1) | US8383574B2 (en) |
| EP (1) | EP2253695B1 (en) |
| JP (1) | JP5270194B2 (en) |
| ES (1) | ES2392318T3 (en) |
| WO (1) | WO2009110433A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012050781A (en) * | 2010-09-03 | 2012-03-15 | Kao Corp | Malodor control agent |
| US9233082B2 (en) | 2010-09-03 | 2016-01-12 | Kao Corporation | Method for searching for malodor control agent, malodor control agent, and malodor control method |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3403641A1 (en) * | 2017-05-15 | 2018-11-21 | Givaudan SA | Fragrance compositions |
| WO2019219227A1 (en) | 2018-05-15 | 2019-11-21 | Givaudan Sa | Organic compounds |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08507314A (en) * | 1992-12-11 | 1996-08-06 | クエスト・インターナショナル・ビー・ブイ | Dimethyl-cyclohexanecarboxylic acid ester in perfume production |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3396097B2 (en) | 1994-10-06 | 2003-04-14 | 長谷川香料株式会社 | Method for producing 4-isopropylcyclohexanecarboxylic acid ester derivative |
| DE602005022206D1 (en) * | 2004-09-14 | 2010-08-19 | Firmenich & Cie | PARFUMBUILDINGS WITH SAFRANGERUCH |
-
2008
- 2008-03-06 JP JP2008056542A patent/JP5270194B2/en not_active Expired - Fee Related
-
2009
- 2009-03-02 ES ES09716480T patent/ES2392318T3/en active Active
- 2009-03-02 WO PCT/JP2009/053887 patent/WO2009110433A1/en active Application Filing
- 2009-03-02 US US12/921,287 patent/US8383574B2/en active Active
- 2009-03-02 EP EP09716480A patent/EP2253695B1/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08507314A (en) * | 1992-12-11 | 1996-08-06 | クエスト・インターナショナル・ビー・ブイ | Dimethyl-cyclohexanecarboxylic acid ester in perfume production |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012050781A (en) * | 2010-09-03 | 2012-03-15 | Kao Corp | Malodor control agent |
| US9233082B2 (en) | 2010-09-03 | 2016-01-12 | Kao Corporation | Method for searching for malodor control agent, malodor control agent, and malodor control method |
| US9526680B2 (en) | 2010-09-03 | 2016-12-27 | Kao Corporation | Method for searching for malodor control agent, malodor control agent, and malodor control method |
Also Published As
| Publication number | Publication date |
|---|---|
| US20110071070A1 (en) | 2011-03-24 |
| US8383574B2 (en) | 2013-02-26 |
| EP2253695A4 (en) | 2011-08-24 |
| EP2253695B1 (en) | 2012-08-29 |
| EP2253695A1 (en) | 2010-11-24 |
| WO2009110433A1 (en) | 2009-09-11 |
| JP5270194B2 (en) | 2013-08-21 |
| ES2392318T3 (en) | 2012-12-07 |
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